


Cheerleader strap punishment

by benskywalker2169



Series: Anna, cheerleader and amateur Dominatrix [1]
Category: No Fandom, Original Work
Genre: Bondage, Cheerleaders, Cock Rings, Come Eating, F/M, Femdom, Foot Fetish, Foot Massage, Humiliation, Kidnapping, Pegging, Rope Bondage, Strap-Ons, Sweat, Uniform Kink, foot worship
Language: English
Status: In-Progress
Published: 2021-02-08
Updated: 2021-02-08
Packaged: 2021-03-14 03:01:40
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 2,454
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29288754
Author URL: https://archiveofourown.org/users/benskywalker2169/pseuds/benskywalker2169
Summary: Anna's teammates tell her all about their sexual exploits. She decides that one of her "friends", obsessed with her for years, would be easy to lure into a precarious situation.
Series: Anna, cheerleader and amateur Dominatrix [1]
Series URL: https://archiveofourown.org/series/2153622
Kudos: 6





	1. The beginning

Anna was really starting to get pissed off. Out of all of the cheerleaders on the team, Anna was the only one who hadn’t fucked a man yet. And I mean fucked. All the other girls talked about their straps, how powerful it made them feel to make a man bend down and take it from them for once. She couldn’t take it, she needed to find out what she was missing. It took her a while, but eventually she devised a plan that she knew was foolproof. Her test subject was simple. Chris was a little simp for her, always bringing her flowers and gifts on gameday. He was always complimenting her and her body. They had known each other for years at this point and Anna knew how obsessed he was. So the plan was made. For a whole week, she started slowly grooming Chris for his role. Anna answered texts that would usually go unanswered, and started flirting with him more and more each passing day, trying to really make him believe that he was somehow going to get the girl. After their last class together ended on Thursday, Anna pulled Chris over to the side and invited him over to her dorm after practice the next day, giving him a quick kiss on the cheek to seal the deal. After a particularly difficult practice the next day, she texted Chris and told him that they could meet in her room right away. The poor guy almost sprinted across campus to make it in time. When he knocked on Anna's door, she let him in, and he almost fell onto his ass. There she was, staring into his eyes, wearing her stunning red and black latex cheerleader's uniform. Its skirt hung so tantalizingly close to revealing her pussy to him. Anna's long, long legs were dripping with sweat, and she was still looking into Chris's eyes as she slipped out of her shoes. Anna gave a quick 360 degree twirl, and for a split second the skirt slipped up just enough to see her ass. Chris realized he was already hard.

"Well? Like what you see?" she asked, taking a step closer to him, grabbing his chest. He was incredibly aroused, but absolutely terrified of what he thought was about to happen. He had one shot wiht the girl of his dreams. "Do you know what I want right now?" her face was inches away from his now.

"I think so..." he said, realizing that there was no way she hadn't already noticed how rock hard she was. "You want me to fuck you?" Anna paused. She looked at Chris, smiled, and giggled in his face before kissing him.

"Well, not yet! We need to work our way up to it, and practice today was just sooo exhausting. I think I need to take a seat." she plopped down in a chair right next to him, and stretched out her glistening legs. "My feet just hurt so badly...I mean...maybe you could help me out with that?" Chris was blushing now. He expected sex! What was she trying to ask him for? Suddenly, they were right in front of his face. He met her expecting eyes again, and started slowly massaging her feet. "Ohhh, you're just a natural! My feet feel better already. I think you are capable of just a little bit more, however..." Suddenly her feet smacked against Chris's face. He knew exactly what she wanted. Was it really worth it? Then Chris decided he could deal with this for just a little longer, and started kissing and worshiping her feet from underneath. They smelled like the gym, and were already wet with her sweat, but Chris truly believed Anna's words at this point. All he had to do was earn it, even if this was all a little bizarre. Anna let out a light moan as he licked up and down her feet, encouraging him. He wasn't exactly sure how long he kept at it, but eventually she slowly pulled her feet away.

"Look up at me, Chris! I think you've finally deserved your reward, what you really want" Chris snapped to attention as Anna pulled out a small canister from under her skirt. She sprayed a simple spritz of aerosol in Chris's face, and suddenly everything started to fade away....


	2. the main event

As Chris slowly woke up from before, he realized that everything was very, very wrong. Tight ropes bound his wrists together, as well as his ankles. His arms and legs were pulled up behind his back, and those ropes were linked together. He felt a particularly tight pressure at the base of his dick, and was ashamed to realize that he was hard as a rock. It didn't take long to also factor in that he was hanging from the ceiling of Anna's dorm. Mouth ball-gagged, he let out a muffled cry of her name as he tried to turn his neck around the room, unable to see behind him.

"Oh get a fucking grip, I'm right behind you." Anna said. Her sultry, flirty voice was different, it had a new edge to it. She paced around her caught victim so he could see her. Still wearing her striking uniform, she had pulled up the skirt to rest over a massive strap-on. Chris began his best attempt to flail away, trying to move and shake in his bonds but he was wrapped up shockingly well by this first time Mistress. Obviously frantic words had no effect but to send a strand of spit falling out from behind his ball gag. "How big do you think this is, huh? 6 inches? 8 inches? 10 inches? I think it doesn't really matter, you're going to have to take every inch of it anyway. Did you think I was really going to let you fuck me??? After a few days of flirty eyes and nice texts, you thought I would really let you even touch this body you little bitch? We are going to fuck, but you should know by now that I'm going to be fucking you. All my teammates say it's the greatest feeling in the world. Let's see if they're right, huh?" she reared back, and spit right in his face, then giggled at her handiwork. Anna stepped out of Chris's line of sight, running her arm across his naked back as she made her way to the target of her attention. Carefully, delicately, she probed a single finger inside and Chris gasped. The cheerleader cackled out loud with amusement at the man's squirms. Anna was started to take some twisted pleasure in Chris's terror. She could tell that the longer she waited, the more afraid he became. She took her sweet time lubing up the strap, making sure it would enter his hole smoothly the first time. 

'  
"Now now now...I'll make sure to open you up nice and wide!" Anna said, bringing both her hands down to smack his ass. The sharp stinging sensation covered up her first tease, as the head of her strap pushed itself into his asshole. Chris's entire body tensed up as Anna pulled it out almost as quickly as she had slid it in. This continued for a while, Anna pushing the head of her silicone cock in and out of Chris, teasing him with circular motions. But then, she pushed it in and held it there. 

"How are you feeling now, huh? I think my girls were right, this is amazing! I'm so fucking powerful, my strap-on cock has the power to rule your tight little hole. You wanted me to take your virginity, didn't you? You can try and pull away all you want but I'm only going to go deeper bitch boy." Anna was right, Chris just wasn't prepared for this fucking. Even with the lube, the strap-on made him grunt with pain every single time she put it in him. There was no way he could be able to take the whole thing, but Anna just laughed and kept going, keeping a hand inside of her uniform to rub and stimulate her pussy from behind the strap. Just the feeling of dominance seemed to give her some kind of sexual arousal, but she wasn't going to let Chris be the only one to have a good time. Soon, she had him at the midway point. Drool was still coming out of his mouth as he tried to beg for mercy any way he could. Good god, it hurt. But Anna kept going. Deeper and deeper, inch by inch, she kept sliding and sliding her massive cock inside of her unwilling victim. Chris grew louder, her dick sank deeper, and as the domineering cheerleader pushed and pushed, she finally hit her target. His ass cheeks were finally sitting right up against her pelvis. The entire strap was in his little hole. He was completely still, any slight movement would be able to destroy him.

"Well well well, I honestly didn't think you could take all of that! I would say that I'm proud, but I'm not. ...wait, do you actually think that we're done here?" Anna threw her head back and laughed again. "Sorry, but you haven't even gotten fucked yet. But I'm more than excited to show you what it's like." Suddenly, she ripped the dick out of his ass at high speed. Chris gasped loudly again at the squelching lubricant sound, for a split second thinking that despite what she said, he would be ok. He was sorely mistaken. Anna slammed the strap all the way back down his winking asshole, and started to fuck him for real. What she had dreamed about from the first time she was told that catching fuckable men like this was possible. In and out and in and out, Anna pushed and pulled, almost immediately clapping the man's cheeks while he hung from her ceiling. Anna could even feel the pleasure from the back of the strap on pushing against her pussy. For Chris, the pain was overwhelming. Anna just kept going and going. As she continued, her bitch had no choice but to keep taking it over and over again. Eventually, Chris started to realize that the pain of this punishment was receding. Chris's anal muscles were starting to relax. Slowly, Chris realized that the pain had completely dulled, dulled to pleasure. Anna kept going and pleasing herself, but she didn't realize that this assault on the g-spot of her victim had finally started to turn around for him. Chris was still uncomfortable, and still in pain, but the stimulation he felt was unbearably powerful. His face was a mess, tears and spit mingled together as he still moaned and shouted words that Anna completely ignored. With her fingers on her clit, Anna had fallen into this deeply pleasurable pattern as well. Anna looked down, and realized that the cock ring she had tied about Chris's sex was getting tighter and tighter. 

"Oh, you were going to cum without me knowing, huh? That seems awfully rude after the gift I gave you. I heard those screams become moans you little slut! You can't help yourself but enjoy this." Mercifully, she stopped. Taking a second to admire the damage done to his hole as it winked and blinked, trying to regain its shape. She couldn't just leave it unaccounted for, could she? Anna unbuckled her strap, and shoved it right down to the end in his asshole. Then, she grabbed Chris by the dick. "You really want to orgasm? I mean, can that little thing even cum? I hadn't really looked at it before, but wow! My strap-on is absolutely bigger than your cock! I don't know how that makes you feel, but I would be absolutely humiliated. But seeing as that mine is silicone and yours is real, I thought you would be able to donate this load to me. And I know you couldn't cum without me in your ass, and I certainly don't blame you for that. But I think I'm going to help you out, too. I've had such a great time, had so much pleasure thanks to you. I guess I should pay you back..." Anna stroked Chris's dick with passion, holding one hand out underneath his head. It was basically bliss for Chris compared to the rest of the events of the day. He was afraid of what it would go to use for, but there was no holding back. Her sexual prowess was unmatched, and it didn't take long for his dick to explode, firing a sizeable load directly into Anna's hand. She stood up, and walked around to face him again. "Now Chris, how did you think this would end? Your new cheerleader girlfriend sucking on your dick, letting you explode all over my latex clad tits? My beautiful face? In my mouth? Well...I'm curious to say the least. I've had to swallow so many loads from men so much hotter than you, I just wonder how the other side would handle it. This has been very enlightening so far..." Then, with one hand Anna reached around his mouth, and removed his ball gag. Chris took a large breath of air, was able to get himself under control, but he looked up at Anna and realized he was speechless. No last words, no pleading, no begging for anything but this. He was simply stunned by her beauty. Anna took her hand, and forced the load of cum into his mouth. She held her hand in there, making sure that he was properly licking up the cum. She pulled her hand out, looked at it, and rubbed the warm spit and whatever was left of the cum across Chris's face. 

"Well, well, well, bitch. Would you look at the time? My night practice is in just an hour. Obviously, there's nothing you could ever deserve to see anything more than the faintest tease of my naked body, so I won't release you while I shower. I know your class schedule anyway. You're free all night, and it's not like you're up early tomorrow anyway. I'll leave you hanging right here, and when I come back later tonight, I think I'm going to be even more sweaty. Now that you understand what I want this arrangement to be, I think you'll do just fine" She laughed in his face again, twirling around and lifting up her skirt so slightly that his eyes darted downwards looking for her ass. Then, Anna walked out of the main room, leaving Chris hanging there. This was the last time he ever trusted a cheerleader again...


End file.
